Cornforth reagent → HCID 58109176, compound

HRID 2037598Notes

Reaction equation

HRID 2037598 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:16][CH2:17][CH2:18][OH:19])[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:16][CH2:17][CH:18]=[O:19])([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 59532370(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxy-propyl)-1,3-oxazinan-2-one

Product 1

HCID 58109176HCID 58109176, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxy-propyl)-1,3-oxazinan-2-one (500 mg, 1.15 mmol), PDC (870 mg, 2.30 mmol) and 3 Å molecular sieves (1.3 g) in methylene chloride was stirred at room temperature for 3 hours. The reaction mixture was chromatographed on silica gel directly to give 3-((R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanal (300 mg, 60%). 1H NMR: (400 MHz, CDCl3): 1.43 (d, 2H), 2.10 (m, 2H), 2.19 (m, 3H), 2.67 (m, 1H), 2.86 (m, 1H), 5.54 (q, 1H), 6.75 (d, 2H), 7.00 (t, 2H), 7.17 (m, 4H), 9.60 (s, 1H).

Workup

  1. customThe reaction mixture was chromatographed on silica gel directly

Sources & evidence

ORD record
ord-41a3ced176274eb0af4d7fee51d17803
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…